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[ CAS No. 29681-43-4 ] {[proInfo.proName]}

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Chemical Structure| 29681-43-4
Chemical Structure| 29681-43-4
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Product Details of [ 29681-43-4 ]

CAS No. :29681-43-4 MDL No. :MFCD00956223
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OJDKENGKKYVJLY-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :1519345
Synonyms :

Calculated chemistry of [ 29681-43-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.01
TPSA : 48.42 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 1.01
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : 0.08
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 1.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.68
Solubility : 3.45 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (Ali) : -1.62
Solubility : 4.05 mg/ml ; 0.0242 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.22
Solubility : 1.0 mg/ml ; 0.00601 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 29681-43-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29681-43-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 29681-43-4 ]
  • Downstream synthetic route of [ 29681-43-4 ]

[ 29681-43-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 29681-43-4 ]
  • [ 16744-81-3 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 8, p. 2074 - 2077
[2] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
  • 2
  • [ 29681-43-4 ]
  • [ 10201-73-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
[2] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 17, p. 2012 - 2021
[3] Organic Preparations and Procedures International, 1997, vol. 29, # 1, p. 117 - 122
[4] Patent: EP2314588, 2011, A1,
  • 3
  • [ 98-98-6 ]
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 29681-43-4 ]
YieldReaction ConditionsOperation in experiment
26%
Stage #1: With thionyl chloride In water at 0℃; for 97 h; Reflux
Stage #2: Reflux
Stage #3: for 48 h; Reflux
To a cooled (0 °C) solution of picolinic acid (5.0 g, 40.6 mmol) in SOCl2 (15 mL) was carefully added H2O (950 μL), and the mixture was refluxed for 1 hr. SOCl2 (15 mL) was added at rt and the mixture was refluxed for 2 days. SOCl2 (15 mL) was added at rt and the mixture was refluxed for further 2 days. After removal of the solution under reduced pressure, the residue was dissolved in MeOH (30 mL) and the mixture was refluxed overnight. A solution of NaOMe (4.4 g, 81.2 mmol) in MeOH (50 mL) was added and the mixture was refluxed for further 2 days. After removal the solvent under reduced pressure, the residue was dissolved in water and extracted with CHCl3. The extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on SiO2 (hexane :AcOEt = 1 : 1 → 1: 4 → 1 : 10) to give a solid. This material was washed with hexane-Et2O (1 : 1) to give 16 (1.8 g, 26 percent) as a pale yellow solid.
Reference: [1] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
  • 4
  • [ 67-56-1 ]
  • [ 29681-43-4 ]
YieldReaction ConditionsOperation in experiment
100% at 60℃; for 36 h; A solution of methyl 4-chloro-2-pyridinecarboxylate hydrochloride (2.0 g, 9.7 mmol) in MeOH (25 ml.) was stirred at 600C for 36 h. The MeOH was removed on the rotovap, and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to generate the title compound of Step A as a white crystalline solid in quantitative yield (1.6 g, 9.7 mmol). 1H NMR (400 MHz, DMSO-d6j: δ 8.48 (d, 1 H, J = 5.7 Hz), 7.51 (d, 1 H, J = 2.8 Hz), 7.19 (dd, 1 H, J = 2.6 Hz, 5.7 Hz), 3.87 (s, 3H), and 3.84 (s, 3H).
Reference: [1] Patent: WO2009/32667, 2009, A1, . Location in patent: Page/Page column 185
  • 5
  • [ 98-98-6 ]
  • [ 67-56-1 ]
  • [ 29681-43-4 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 23, p. 5562 - 5565
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
[3] Organic and Biomolecular Chemistry, 2006, vol. 4, # 6, p. 1071 - 1084
  • 6
  • [ 67-56-1 ]
  • [ 53750-66-6 ]
  • [ 29681-43-4 ]
Reference: [1] Organic Preparations and Procedures International, 1997, vol. 29, # 1, p. 117 - 122
[2] Patent: EP2314588, 2011, A1, . Location in patent: Page/Page column 16-17
  • 7
  • [ 29745-44-6 ]
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 29681-43-4 ]
Reference: [1] Patent: US7081461, 2006, B1, . Location in patent: Page/Page column 45
  • 8
  • [ 86251-47-0 ]
  • [ 29681-43-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 477 - 478
  • 9
  • [ 17209-50-6 ]
  • [ 29681-43-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 477 - 478
  • 10
  • [ 98-98-6 ]
  • [ 29681-43-4 ]
Reference: [1] Patent: EP2314588, 2011, A1,
  • 11
  • [ 29745-44-6 ]
  • [ 67-56-1 ]
  • [ 29681-43-4 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 33, p. 6411 - 6420
  • 12
  • [ 67-56-1 ]
  • [ 64197-01-9 ]
  • [ 29681-43-4 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 3, p. 435 - 437
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